Sodium Bicarbonate → Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate

HRID 1382114Notes

Reaction equation

HRID 1382114 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10]([CH2:12]Cl)=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:14][C:15]([NH2:17])=[S:16].C([O-])(=O)C.[Na+].C(=O)(O)[O-].[Na+]>CO.O>[CH3:1][O:2][N:3]=[C:4]([C:10]1[N:14]=[C:15]([NH2:17])[S:16][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 3017525Ethyl 4-chloro-2-(methoxyimino)-3-oxobutanoate

Product 1

HCID 581091Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetateYield 68.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-methoxyimino-4-chloroacetoacetate (syn isomer) (50 g.) was added over 3 minutes with stirring at ambient temperature to a solution of thiourea (18.4 g.) and sodium acetate (19.8 g.) in a mixture of methanol (250 ml.) and water (250 ml. ). After stirring for 35 minutes at 40° to 45° C., the reaction mixture was cooled with ice and adjusted to pH 6.3 with a saturated aqueous solution of sodium bicarbonate. After stirring for 30 minutes at the same temperature, precipitates were collected by filtration, washed with water (200 ml.) and then with diisopropyl ether (100 ml.), and dried to give colorless crystals of ethyl 2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetate (syn isomer) (37.8 g.), mp 161° to 162° C.

Workup

  1. temperaturethe reaction mixture was cooled with ice
  2. stirringAfter stirring for 30 minutes at the same temperature
  3. customprecipitates
  4. filtrationwere collected by filtration
  5. washwashed with water (200 ml.)
  6. dry with materialwith diisopropyl ether (100 ml.), and dried

Sources & evidence

ORD record
ord-dfcc9aac0f2b49788c82452a3e21dab2
Source dataset
uspto-grants-1989_02
Patent number
US04804752

Reaction notes

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